Since there seems to be more male riders than female riders, men might find it difficult to find a fellow female cyclist. Besides, there also are quite a few type of cyclists -- fast movers vs leasurely cyclists, for example. I suspect that riding with some nice stop point along the way might help, because it's much easier to hold a conversation while sitting in a park (with bike near you, maybe), than it is while riding.
But one never really knows how things happen. A little over 10 years ago, I met a lovely woman in the metro (our public rapid transit). She is now my wife and we have 2 daughters.
Regards,